EP3959993A1 - Verfahren zur lösungsmittelfreien herstellung von aromakonzentraten - Google Patents

Verfahren zur lösungsmittelfreien herstellung von aromakonzentraten Download PDF

Info

Publication number
EP3959993A1
EP3959993A1 EP20192328.1A EP20192328A EP3959993A1 EP 3959993 A1 EP3959993 A1 EP 3959993A1 EP 20192328 A EP20192328 A EP 20192328A EP 3959993 A1 EP3959993 A1 EP 3959993A1
Authority
EP
European Patent Office
Prior art keywords
potassium
sodium
water steam
adsorbent
sulfate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP20192328.1A
Other languages
English (en)
French (fr)
Other versions
EP3959993B1 (de
Inventor
Stefan Brennecke
Johannes KIEFL
Martin HEINEMEIER
Tanja LANGNER
Claudia UTERMÖHLE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Priority to PT201923281T priority Critical patent/PT3959993T/pt
Priority to PL20192328.1T priority patent/PL3959993T3/pl
Priority to EP20192328.1A priority patent/EP3959993B1/de
Priority to ES20192328T priority patent/ES2940292T3/es
Publication of EP3959993A1 publication Critical patent/EP3959993A1/de
Application granted granted Critical
Publication of EP3959993B1 publication Critical patent/EP3959993B1/de
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
    • A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
    • A23L5/273—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption using adsorption or absorption agents, resins, synthetic polymers, or ion exchangers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/115—Natural spices, flavouring agents or condiments; Extracts thereof obtained by distilling, stripping, or recovering of volatiles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/265—Adsorption chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
    • B01D15/3861—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36 using an external stimulus
    • B01D15/3876—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36 using an external stimulus modifying the temperature
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
    • B01D53/025—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with wetted adsorbents; Chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
    • B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
    • B01D53/0462—Temperature swing adsorption
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/20—Organic adsorbents
    • B01D2253/206—Ion exchange resins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
    • B01D2257/702—Hydrocarbons
    • B01D2257/7027—Aromatic hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2259/00—Type of treatment
    • B01D2259/40—Further details for adsorption processes and devices
    • B01D2259/40083—Regeneration of adsorbents in processes other than pressure or temperature swing adsorption
    • B01D2259/40088—Regeneration of adsorbents in processes other than pressure or temperature swing adsorption by heating
    • B01D2259/4009—Regeneration of adsorbents in processes other than pressure or temperature swing adsorption by heating using hot gas

Definitions

  • the present invention relates to a method for producing an aroma concentrate of a liquid composition, comprising one or more aromatic substance(s).
  • Aromatizing foodstuff of any kind has become ever-present and is made use of for decades. Adding aromatic substances to any kind of foodstuff can have several reasons, such as compensating for loss of aromatic substances during production, storage and preparation of the foodstuff, or for imparting a particular taste to a foodstuff. Without aromatization, the plenty of today's foodstuffs could not be imagined and furthermore, adding aromatic substances to foodstuff enables consistent taste impressions of specific products overtime.
  • the source of natural aromatic substances are natural products such as (parts of) plants, fruits or vegetables.
  • the extraction of raw materials with supercritical carbon dioxide is the standard process for obtaining aroma oils.
  • a particular relevance on an industrial level is particularly found in extracts of solid raw materials such as bark, roots, rhizomes, leaves, blossoms and fruits, all of which already have a high concentration of aromatic substances, which may be in the range of several percent.
  • the primary object of the present invention was thus to provide an improved method for obtaining aromatic substances from liquid and gaseous raw materials. Further objects underlying the present invention become apparent when studying the following description, including examples and the advantageous effects mentioned therein.
  • the primary object of the present invention is achieved by a method for producing an aroma concentrate of a liquid or gaseous composition, comprising one or more aromatic substance(s), comprising or consisting of the following steps:
  • thermal desorption describes a principle well known to a skilled person and involves collecting volatile organic compounds onto a sorbent, and then heating this sorbent in a flow of gas to release the compounds and concentrate them into a smaller volume.
  • the method according to the invention results in an aroma concentrate, which has two different phases, a water phase and an oil phase.
  • a water phase As many aromatic substances are water insoluble or sparingly soluble in water, the presence of a (separate) oil phase - including many aromatic substances - indicates a large concentration of aromatic substances in the obtained aroma concentrate.
  • the experiments with a different absorber material did not provide an aroma concentrate with two separate phases (see Example 1 below). This indicates that the concentration of the aromatic substances in said sample is not high enough to form a (separate) oil phase.
  • the method according to the invention thus provides aroma concentrates with particularly high amounts of aromatic substances.
  • the oil phase obtained by a method according to the invention comprises mostly nonpolar and medium-polar aromatic substances.
  • liquid or gaseous composition provided in step a) is of plant, animal or fungal origin or a combination of compositions of plant and/or animal and/or fungal origin.
  • a liquid or gaseous composition as described herein may be selected for example from fruits, herbs, spices, vegetables, and meat aqueous extracts or enzymatically treated / fermented organic products.
  • the adsorbent is contained in a column particularly constructed for the intended purpose and well known in the state of the art.
  • the column size is usually indicated by its volume.
  • a column which may be used in a method according to the invention, may be of any size, as an example, a column with a size of 2 L may be used.
  • the setup to be used for a method according to the invention includes one or more columns, wherein in case more than one column is used, these columns may have the same or a different size. The columns may be used simultaneously or subsequently in a method according to the invention.
  • FIG. 1 An exemplary experimental setup to be used for a method according to the invention is shown in Fig. 1 .
  • WO 2015/104357 describes the desorption of adsorber resins with water steam for obtaining an aroma concentrate.
  • the precise process parameters e.g. temperature or water steam flux
  • the obtained sample only represents 3 to 30 wt.-% of the original beverage and the presence of an oil phase is not described.
  • the enrichment factor of 3 to 30 is not sufficient in case the sample shall be further processed by distillation for standardizing the process. It would be ideal for this case to obtain a sample, which is reduced or substantially free of water or further solvents, i.e. an oil phase.
  • the aroma concentrate comprises a water phase and an oil phase, comprising the, one, more or all of the one or more aromatic substance(s), wherein the method further comprises the step e) separating the oil phase to obtain an aroma oil comprising the, one, more or all of the one or more aromatic substance(s).
  • the separation of an oil and a water phase may as an example be performed using a separating funnel.
  • An important advantage of obtaining such an oil phase is that - compared to aqueous concentrates or concentrates containing solvents - the oil phases are more stable and do not form acetals and can be applied to both, aqueous and oily systems.
  • the obtained aroma concentrates cannot exceed the legal limits of solvent concentrations.
  • the obtained aroma concentrates can be declared as halal, kosher and/or FTNF (from the named fruit).
  • the adsorbent may be selected from the following list, wherein the adsorbents with corresponding names (exemplary adsorbent) but different numbers may differ in e.g. pore diameter, pore volume and/or surface area from each other: Material Exemplary adsorbent 1 Manufacturer Polystyrene cross-linked with divinyl benzene Purosorb PAD 350 Purolite Polystyrene cross-linked with divinyl benzene Purosorb PAD 400 Purolite Polystyrene cross-linked with divinyl benzene Purosorb PAD 550 Purolite Polystyrene cross-linked with divinyl benzene Purosorb PAD 600 Purolite Polystyrene cross-linked with divinyl benzene Purosorb PAD 900 Purolite Polystyrene Purosorb PAD 910 Purolite Polystyrene cross-linked with divinyl benzene Purosorb PAD 1200 Purolite Polystyrene
  • the term "macroporous” as used herein describes a material with pores having an average pore size of more than 2 nm, preferably a pore size of from 5 to 110 nm.
  • the average pore size is the measured or calculated average over the size of all pores in the material. Methods for determining the pore size are well-known and include e.g. the Hg intrusion method.
  • microporous as used herein describes a material with pores having an average pore size of less than 2 nm, preferably 1 nm.
  • the average pore size is the measured or calculated average over the size of all pores in the material. Methods for determining the pore size are well-known and include e.g. the Hg intrusion method.
  • the concentration of aromatic substances in the oil phase was particularly high if the adsorbent is heated to a temperature in the range of from 110 °C to 170 °C during the thermal desorption, and especially for a temperature in the range of from 120 °C to 150 °C before the water steam is applied (see Example 2 below).
  • step c) the adsorbent is heated to a temperature in the range of from 120 °C to 150 °C, further preferably in the range of from 140 °C to 150 °C before the water steam is applied.
  • the adsorbent itself is heated by one or more heating element(s) before the water steam is applied.
  • the one or more heating element(s) can be positioned outside and/or inside the column comprising the adsorbent.
  • the temperature of the water steam applied in step c) can be important.
  • the water steam applied in step c) has a temperature in the range of from 120 °C to 180 °C, preferably in the range of from 130 °C to 160 °C, further preferably in the range of from 150 °C to 160 °C.
  • the water steam applied in step c) preferably has a temperature which is 5 to 15 °C, preferably 7.5 to 12.5 °C, particularly preferably 10 °C higher than the temperature to which the adsorbent is heated to before the water steam is applied.
  • the concentration of aromatic substances in the oil phase was particularly high if the thermal desorption comprises a step of applying water steam to the adsorbent with a water steam flux of up to 20 g/min, based on a 2.0 L column (see Example 3 below).
  • the water steam flux in step c) is in a range of from 5 g/min to 10 g/min, based on a 2.0 L column.
  • a 2.0 L column is meant to be understood such that a column including the adsorbent is used / provided and that the inner volume of the column is 2.0 L. Typically, the inner volume of the column is substantially filled with the adsorbent.
  • a water steam flux of 20 g/min, based on a 2.0 L column (the following applies for other values of the steam flux accordingly) is understood such that a column with an inner volume of 2.0 L is used / provided. Typically, the inner volume of the column is substantially filled with the adsorbent. To said column, water steam is applied in a flux of 20 g/min. A skilled person knows that the effect of the same water steam flux is different depending on the volume of the used column.
  • a "water steam flux of 20 g/min, based on a 2.0 L column” not only includes the particular 20 g/min in the particular 2.0 L column, but also a flux in a column of a different volume, which would correspond to the 20 g/min if the used column would have a volume of 2.0 L.
  • the flux changes proportionally to the volume of the column.
  • the step of applying water steam to the adsorbent is downstream of the steps of loading the adsorbent with the liquid composition, rinsing the adsorbent at least once, preferably at least twice, with a mobile phase, e.g. water, and drying the adsorbent with nitrogen.
  • a mobile phase e.g. water
  • the drying step only reduces the amount of the mobile phase but does not completely remove it.
  • the term "applying water steam to the adsorbent with a water steam flux of up to 50g/min, based on a 2.0 L column” may also include a water steam flux of 0 g/min, based on a 2.0 L column, if a thermal desorption with residual water can be performed after incomplete drying step (i.e. the mobile phase is not completely removed). In this way, the amount of applied water can be reduced to a minimum.
  • the applied water steam comprises one or more solvents, preferably organic solvents. It was found that such solvents may have an impact on the aromatic profiles of the obtained aroma concentrates or, respectively, aroma oils and can thus be used to distinctly modify said aromatic profiles.
  • an apple aroma for example, that it was particularly advantageous if the total amount of aromatic substances in the aroma concentrate was at least 5000 ppm, preferably at least 10,000 ppm. This amount may also apply to other aromas. However, it can also be different in other aromas.
  • the parameters temperature, water steam flux (based on a 2.0 L column) and pressure are selected according to the following table: Temperature adsorbent [°C] Temperature applied water steam [°C] Water steam flux [g/min] Maximum pressure [bar] Applied pressure [bar] 120 130 5 0.9 0.7 130 140 5 1.7 1.4 140 150 5 2.3 1.9 150 160 5 3.4 3.0 160 170 5 5.1 4.6 170 180 5 6.6 6.1 120 130 10 1.3 1.0 130 140 10 2.0 1.7 140 150 10 2.7 2.4 150 160 10 3.8 3.4 160 170 10 5.5 5.0 170 180 10 6.9 6.4 120 130 20 1.5 1.2 130 140 20 2.6 2.3 140 150 20 3.2 2.9 150 160 20 4.8 4.4 160 170 20 6.0 5.5 170 180 20 7.5 7.0
  • Temporal adsorbent in the above table describes the temperature to which the adsorbent is heated before the water steam is applied.
  • Temporal applied water steam in the above table describes the temperature of the water steam that is to be applied on the adsorbent.
  • the actual temperature of the water steam when directly in contact with the adsorbent may slightly differ from the indicated temperature.
  • Applied pressure in the above table describes the pressure present at the adsorbent.
  • a closed system is used for the desorption with the water steam.
  • the "Applied pressure” is the pressure, which shall be kept constant by the control valve present in this system during the desorption.
  • the "Applied pressure” can be determined.
  • the term “Maximum pressure” is the pressure, which sets in when applying the other parameters without opening the back pressure valve present in this system.
  • the “Maximum pressure” is lower then the theoretical vapour pressure for the respective temperature. This can be explained by that the system is not perfectly closed for gas due to the control valve.
  • the "Applied pressure” is determined as 0.2 to 0.6 bar lower than the "Maximum pressure”.
  • a salt preferably a salt selected from the group consisting of calcium carbonate, sodium carbonate, potassium carbonate, ammonium carbonate, sodium chloride, potassium chloride, calcium chloride, magnesium chloride, tin(ii)-chloride, sodium sulfate, potassium sulfate, ammonium sulfate, aluminium sulfate, aluminium sodium sulfate, aluminium potassium sulfate, aluminium ammonium sulfate, potassium acetate, sodium acetate, calcium acetate, sodium propionate, calcium propionate, potassium propionate, sodium lactate, potassium lactate, calcium lactate, sodium citrate, potassium citrate, triammonium citrate, sodium tartrate, potassium tartrate, sodium-potassium tartrate, sodium phosphate, potassium phosphate, diphosphate (Na), triphosphate (Na), polyphosphate, sodium malate, potassium malate, sodium adipate, potassium adipate, or a
  • the, one, two, three or more salt(s) can be selected from the following list: Salt E-Number Formula Solubility in water (%) Molar Mass (g/mol) Calcium carbonate E 170 CaCO 3 14.0 100.1 Sodium carbonate E 500 Na 2 CO 3 21.7 106.0 Potassium carbonate E 501 K2CO3 112 138.2 Ammonium carbonate E 503 (NH 4 ) 2 CO 3 32.0 96.1 Sodium chloride NaCl 36.0 58.4 Potassium chloride E 508 KCI 34.7 74.6 Calcium chloride E 509 CaCl 2 74.0 111.0 Magnesium chloride E 511 MgCl 2 54.2 95.2 Tin(II)-chloride E 512 SnCl 2 270.0 189.6 Sodium sulfate E 514 Na 2 SO 4 17.0 142.0 Potassium sulfate E 514 K2SO4 11.0 174.3 Ammonium sulfate E 517 (NH 4 ) 2 SO 4 75.4 132.1 Aluminium
  • the method according to the invention further comprises the step f) adding a salt, preferably a salt selected from the group consisting of calcium carbonate, sodium carbonate, potassium carbonate, ammonium carbonate, sodium chloride, potassium chloride, calcium chloride, magnesium chloride, tin(ii)-chloride, sodium sulfate, potassium sulfate, ammonium sulfate, aluminium sulfate, aluminium sodium sulfate, aluminium potassium sulfate, aluminium ammonium sulfate, potassium acetate, sodium acetate, calcium acetate, sodium propionate, calcium propionate, potassium propionate, sodium lactate, potassium lactate, calcium lactate, sodium citrate, potassium citrate, triammonium citrate, sodium tartrate, potassium tartrate, sodium potassium tartrate, sodium phosphate, potassium phosphate, diphosphate (Na), triphosphate (Na), polyphosphate, sodium malate, potassium malate, sodium adipate,
  • a salt
  • a salt may be added before the phases are separated or to the water phase, after separating the oil phase in step e).
  • a flow chart for an exemplary setting can be seen in Figure 8 .
  • a salt may also be added before the phases are separated and to the water phase, after separating the oil phase in step e).
  • the salt may be the same or different.
  • the term "different" also includes the case that one of the salts is a combination of the salts specified herein and the other salt is either no combination or not the same combination of the salts specified herein.
  • the last stage of the method, in which the aroma concentrate is obtained, can also be performed in a way to obtain several fractions of the aroma concentrate (i.e. the fractions are aroma concentrates themselves).
  • steps c) to d) or, each where applicable, to e) or to f) are performed at least 2 times, at least 3 times, at least 4 times, at least 5 times, at least 6 times, at least 7 times, at least 8 times, at least 9 times, at least 10 times or more than 10 times, for obtaining 2, 3, 4, 5, 6, 7, 8, 9, or, respectively, 10 or more aroma concentrates or, respectively, aroma oils.
  • the volume of the obtained fractions may be the same or may differ between one or more of the fractions.
  • the volume of the obtained fractions is in a range of from 0.5 to 30 % of the volume of the column used.
  • the volume of the obtained fractions is 2 %, preferably 5 %, further preferably 10 %, also preferably 20 %, each of the volume of the column used.
  • a volume of the obtained fractions of 5 % amounts to 100 mL.
  • the "volume of the column used" refers to the particular column(s) from which the respective fraction(s) is/are obtained. If the respective fraction(s) is/are obtained from more than one column, the "volume of the column used” refers to the sum of the volumes of these columns.
  • the temperature, to which the adsorbent is heated to in step c) before the water steam is applied varies between two, three, four or more or all of the performances of step c).
  • the temperature of the water steam applied in step c) varies between two, three, four or more or all of the performances of step c).
  • the water steam flux in step c) varies between two, three, four or more or all of the performances of step c).
  • An exemplary procedure includes the following steps after step d) of the method according to the invention:
  • Example 1 Influence of the adsorbent material
  • Adsorbent Aroma load 1 Activated carbon (70 g) 3.5 g (50 mg/g activated carbon) 2 147 g Cross-linked polystyrene 4.4 g (30 mg/g Cross-linked polystyrene)
  • the two adsorbent were provided according to the above table and loaded with apple aroma as indicated.
  • the volume flux for loading was 20 ml/min.
  • the adsorbent had a volume of 2 L and was loaded with 50 kg apple aroma.
  • Cross-linked polystyrene was used as adsorbent material.
  • the volume flux for loading the adsorbent was 300 ml/min.
  • the adsorbent was heated to the following temperature before applying the water steam: Approach Temperature [°C] 1 120 2 130 3 140 4 150
  • the temperature of the applied water steam was 10 °C higher than the temperature indicated in the above table.
  • the water steam flux was 10 g/min and was applied for 100 min.
  • the adsorbent is eluted with ethanol (50 ml/min) to eluate the aromatic substances which are not volatile in water steam.
  • the first 300 to 400 ml of obtained liquid are discharged as they represent the remaining moisture of the adsorbent without aromatic substances.
  • the subsequently obtained ethanolic liquid contains the aromatic substances which are not volatile in water steam and has a volume of approximately 1600 ml.
  • the percentage recovery of the aromatic substances in the oil phase obtained due to thermal desorption with the water steam
  • the phase eluted with ethanol is presented.
  • the adsorbent had a volume of 2 L and was loaded with 50 kg apple aroma.
  • Cross-linked polystyrene was used as adsorbent material.
  • the volume flux for loading the adsorbent was 300 ml/min.
  • the adsorbent was heated to 150 °C, the temperature of the applied water steam was 160 °C.
  • the adsorbent is eluted with ethanol (50 ml/min) to eluate the aromatic substances which are not volatile in water steam.
  • the first 300 to 400 ml of obtained liquid are discharged as they represent the remaining moisture of the adsorbent without aromatic substances.
  • the subsequently obtained ethanolic liquid contains the aromatic substances which are not volatile in water steam and has a volume of approximately 1600 ml.
  • the percentage recovery of the aromatic substances in the oil phase obtained due to thermal desorption with the water steam
  • the phase eluted with ethanol is presented.
  • Example 4 Obtaining a second oil phase
  • the adsorbent had a volume of 2 L and was loaded with 50 kg apple water phase.
  • Cross linked polystyrene was used as adsorbent material.
  • the volume flux for loading the adsorbent was 300 ml/min.
  • the adsorbent was heated to 150 °C, the temperature of the applied water steam was 160 °C.
  • the water steam flux was 10 g/min and was applied for 100 min.
  • the water phase was treated with 83.3 % NaCl, based on the theoretical solubility of NaCl in water.
  • a second oil phase was separated and was collected.
  • Example 4 was performed as described, however, NaCl was added to the water phase after phase separation as indicated in the following table: Approach NaCl [%, based on the theoretical solubility of NaCl in water] 1 0 2 27.8 3 41.67 4 55.56 5 69.44 6 83.33
  • the adsorbent had a volume of 2 L and was loaded with 50 kg apple aroma.
  • Cross-linked polystyrene was used as adsorbent material.
  • the volume flux for loading the adsorbent was 300 ml/min.
  • the adsorbent was heated to 150 °C, the temperature of the applied water steam was 160 °C
  • the water steam flux was 10 g/min and was applied ten times for 10 min each.
  • Hexenal/Hexenol block Proportion [%] Fraction trans- 2-hexenol, trans -2-hexenal cis- 3-hexenol trans -3-hexenol 1 2.8 12.7 2.2 4.1 2 4.6 20.0 3.6 7.8 3 6.0 18.9 4.7 12.1 4 7.2 16.4 5.5 11.5 5 8.5 11.9 6.9 8.5 6 11.3 7.9 10.4 10.6 7 14.6 5.4 14.2 10.2 9 21.0 3.7 23.8 15.2 10 24.1 3.1 28.8 20.1
  • Fraction Sensory impression 1 Ester, fruity, , ripe, apple, very juicy, green 2 Ester, fruity, slightly more green, more body / fullness 3 Ester, fruity, slightly like green apple 4 More flat, like skin, fruity, apple shell, red apple 5 Flat, like skin, slightly fruity 6 Green, like skin, fruity, apple skin, slightly fermented 7 Flat, apple skin, slightly like plum 8 Weak, slightly green, apple puree, slightly woody 9 Green, apple skin, apple juice, fruity, juicy 10 Green, apple skin, slightly fermented, fruity, juicy eluate Green, like fusel, heavy fruity, apple puree, similar to fraction 10 but weaker
  • fractions 1-4 had a sensory profile dominated by green and fresh impressions, fractions 5-6 were dominated by apple skin impressions and fermented, fusel-like notes dominated fractions 7-10 and the eluate.
  • Fraction Sensory impression 1-4 Lively, ester, fruity, apple juice, slightly green, juicy 5-6 Skin impressions / apple skin, flaky, cooked note, green, slightly ester, slightly fruity, mouthfeel, impact 7-10 Apple puree, cooked apple, slightly fusel-likenote
  • the different fractions show different sensory impressions.
  • the sensory profile of the obtained aroma concentrate(s) can be controlled.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP20192328.1A 2020-08-24 2020-08-24 Verfahren zur lösungsmittelfreien herstellung von aromakonzentraten Active EP3959993B1 (de)

Priority Applications (4)

Application Number Priority Date Filing Date Title
PT201923281T PT3959993T (pt) 2020-08-24 2020-08-24 Método para a produção de concentrados de aroma sem solventes
PL20192328.1T PL3959993T3 (pl) 2020-08-24 2020-08-24 Sposób wytwarzania niezawierających rozpuszczalnika koncentratów aromatów
EP20192328.1A EP3959993B1 (de) 2020-08-24 2020-08-24 Verfahren zur lösungsmittelfreien herstellung von aromakonzentraten
ES20192328T ES2940292T3 (es) 2020-08-24 2020-08-24 Procedimiento para la producción de concentrados aromáticos sin disolventes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP20192328.1A EP3959993B1 (de) 2020-08-24 2020-08-24 Verfahren zur lösungsmittelfreien herstellung von aromakonzentraten

Publications (2)

Publication Number Publication Date
EP3959993A1 true EP3959993A1 (de) 2022-03-02
EP3959993B1 EP3959993B1 (de) 2022-12-14

Family

ID=72234670

Family Applications (1)

Application Number Title Priority Date Filing Date
EP20192328.1A Active EP3959993B1 (de) 2020-08-24 2020-08-24 Verfahren zur lösungsmittelfreien herstellung von aromakonzentraten

Country Status (4)

Country Link
EP (1) EP3959993B1 (de)
ES (1) ES2940292T3 (de)
PL (1) PL3959993T3 (de)
PT (1) PT3959993T (de)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2631225A1 (de) * 1976-07-12 1978-01-26 Adsorptionstech Lab Regenerieren beladener adsorptionsmittel mit wasserdampf
DE3030967A1 (de) 1980-08-16 1982-03-18 Daimler-Benz Ag, 7000 Stuttgart Verfahren zur desorption von aktivkohle mittels wasserdampf
EP2075320A1 (de) 2007-12-17 2009-07-01 Symrise GmbH & Co. KG Verfahren zur Herstellung eines Aromakonzentrates sowie ein Aromakonzentrat
WO2015104357A1 (de) 2014-01-10 2015-07-16 Wia Wine Ag Vorrichtung und verfahren zur herstellung eines entalkoholisierten getränks

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2631225A1 (de) * 1976-07-12 1978-01-26 Adsorptionstech Lab Regenerieren beladener adsorptionsmittel mit wasserdampf
DE3030967A1 (de) 1980-08-16 1982-03-18 Daimler-Benz Ag, 7000 Stuttgart Verfahren zur desorption von aktivkohle mittels wasserdampf
EP2075320A1 (de) 2007-12-17 2009-07-01 Symrise GmbH & Co. KG Verfahren zur Herstellung eines Aromakonzentrates sowie ein Aromakonzentrat
WO2015104357A1 (de) 2014-01-10 2015-07-16 Wia Wine Ag Vorrichtung und verfahren zur herstellung eines entalkoholisierten getränks

Also Published As

Publication number Publication date
PL3959993T3 (pl) 2023-06-26
ES2940292T3 (es) 2023-05-05
PT3959993T (pt) 2023-03-15
EP3959993B1 (de) 2022-12-14

Similar Documents

Publication Publication Date Title
AU2002304764B2 (en) Stabilized aroma-providing components and foodstuffs containing same
US20110212037A1 (en) Process for producing purified essential oil
JP6761350B2 (ja) 飲料の香味改善方法
JP5922974B2 (ja) 保存性に優れた天然香料の製造方法
WO2015093522A1 (ja) コーヒー濃縮組成物
JP6139219B2 (ja) 容器詰コーヒー飲料
JP2018534049A (ja) 吸着システム及び吸着システムの運転方法
KR102236433B1 (ko) 볶은 커피콩으로부터의 향료 조성물의 제조 방법 및 볶은 커피콩으로부터의 향기 회수 장치
CA2572995C (en) Method for decaffeinating tea
JP5968639B2 (ja) 茶飲料
EP3959993A1 (de) Verfahren zur lösungsmittelfreien herstellung von aromakonzentraten
Paiva et al. Evaluation of the quality of coffee extracts concentrated by osmotic evaporation
US5908652A (en) Method for modifying aroma-containing gas
JP6714502B2 (ja) フルーティー香を増強するためのコーヒー豆の焙煎方法及びコーヒー抽出物の製造方法
Kibar Adsorptive recovery of phenolics from apple juice via batch and fixed bed column
JP6672317B2 (ja) エッセンシャルオイル分画方法
JP7430536B2 (ja) 緑茶飲料
JPH04345693A (ja) 天然香料の劣化防止方法
JP6415981B2 (ja) 単量体プロアントシアニジン除去植物抽出物
JP2003001002A (ja) 液状物の抽出方法
WO2016157984A1 (ja) 飲料又は食品、香料組成物および劣化臭生成抑制方法
JP4383332B2 (ja) 容器詰飲料
NUSS et al. Concentration of onion juice volatiles by reverse osmosis and its effects on supercritical CO2 extraction
JPH03123480A (ja) 食酢の製造方法
KR20170065510A (ko) 폴리페놀의 정제

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17P Request for examination filed

Effective date: 20211221

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

17Q First examination report despatched

Effective date: 20220218

REG Reference to a national code

Ref country code: DE

Ref legal event code: R079

Ref document number: 602020006896

Country of ref document: DE

Free format text: PREVIOUS MAIN CLASS: A23L0005200000

Ipc: B01D0015380000

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

RIN1 Information on inventor provided before grant (corrected)

Inventor name: UTERMOEHLE, CLAUDIA

Inventor name: LANGNER, TANJA

Inventor name: HEINEMEIER, MARTIN

Inventor name: KIEFL, JOHANNES

Inventor name: BRENNECKE, STEFAN

RIC1 Information provided on ipc code assigned before grant

Ipc: B01D 53/02 20060101ALI20220613BHEP

Ipc: B01D 15/26 20060101ALI20220613BHEP

Ipc: B01D 53/04 20060101ALI20220613BHEP

Ipc: A23L 27/10 20160101ALI20220613BHEP

Ipc: A23L 5/20 20160101ALI20220613BHEP

Ipc: B01D 15/38 20060101AFI20220613BHEP

INTG Intention to grant announced

Effective date: 20220628

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE PATENT HAS BEEN GRANTED

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602020006896

Country of ref document: DE

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: AT

Ref legal event code: REF

Ref document number: 1537341

Country of ref document: AT

Kind code of ref document: T

Effective date: 20230115

REG Reference to a national code

Ref country code: PT

Ref legal event code: SC4A

Ref document number: 3959993

Country of ref document: PT

Date of ref document: 20230315

Kind code of ref document: T

Free format text: AVAILABILITY OF NATIONAL TRANSLATION

Effective date: 20230309

REG Reference to a national code

Ref country code: NL

Ref legal event code: FP

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG9D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230314

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2940292

Country of ref document: ES

Kind code of ref document: T3

Effective date: 20230505

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: RS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230315

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SM

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230414

Ref country code: AL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602020006896

Country of ref document: DE

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20230823

Year of fee payment: 4

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20230831

Year of fee payment: 4

Ref country code: ES

Payment date: 20230918

Year of fee payment: 4

Ref country code: CH

Payment date: 20230902

Year of fee payment: 4

26N No opposition filed

Effective date: 20230915

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: PT

Payment date: 20230821

Year of fee payment: 4

Ref country code: PL

Payment date: 20230811

Year of fee payment: 4

Ref country code: FR

Payment date: 20230821

Year of fee payment: 4

Ref country code: DE

Payment date: 20230822

Year of fee payment: 4

REG Reference to a national code

Ref country code: AT

Ref legal event code: UEP

Ref document number: 1537341

Country of ref document: AT

Kind code of ref document: T

Effective date: 20221214

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20221214

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230824

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230824

REG Reference to a national code

Ref country code: BE

Ref legal event code: MM

Effective date: 20230831

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A